10.1021/om0502279.s001
Yumei Luo
Yumei
Luo
James W. Herndon
James W.
Herndon
Tandem Isobenzofuran Formation−Diels Alder Reactions
in the Coupling of Carbene Complexes with
2-Alkynylbenzaldehyde Derivatives Featuring an
Alkyne-Dienophile Tether
American Chemical Society
2005
intramolecular
Carbene Complexes
reaction proceeds
hydrophenanthrene derivatives
carbene complexes
heterocyclic analogues
oxanorbornene ring
2005-06-20 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Tandem_Isobenzofuran_Formation_Diels_Alder_Reactions_in_the_Coupling_of_Carbene_Complexes_with_2_Alkynylbenzaldehyde_Derivatives_Featuring_an_Alkyne_Dienophile_Tether/3281464
The coupling of carbene complexes and 2-alkynylbenzaldehyde derivatives has been
examined for systems where the alkyne is further linked to an alkene. This reaction proceeds
via generation of an isobenzofuran followed by a stereoselective intramolecular Diels−Alder
reaction, followed by opening of the resulting oxanorbornene ring. A variety of hydrophenanthrene derivatives and heterocyclic analogues have been produced in this reaction. In one
case the intramolecular Pauson−Khand reaction is a competing process.